Sodium Iodide → HCID 59252569, compound

HRID 590495Notes

Reaction equation

HRID 590495 reaction equation
[CH2:1]([NH:5][C:6]1[N:14]=[C:13]2[C:9]([N:10]=[C:11]([O:19]C)[N:12]2[CH2:15][CH2:16][CH2:17]Cl)=[C:8]([NH2:21])[N:7]=1)[CH2:2][CH2:3][CH3:4].[NH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1.[I-].[Na+]>C1COCC1>[NH2:21][C:8]1[N:7]=[C:6]([NH:5][CH2:1][CH2:2][CH2:3][CH3:4])[N:14]=[C:13]2[C:9]=1[NH:10][C:11](=[O:19])[N:12]2[CH2:15][CH2:16][CH2:17][N:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 8082PiperidineHCID 59252611N2-Butyl-9-(3-chloropropyl)-8-(methyloxy)-9H-purine-2,6-diamine

Product 1

HCID 59252569HCID 59252569, compoundYield 5.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of N2-butyl-9-(3-chloropropyl)-8-(methyloxy)-9H-purine-2,6-diamine (250 mg, 0.8 mmole), piperidine (340 mg, 4 mmole) and sodium iodide (360 mg, 2.4 mmole) in THF (8 ml) was heated under reflux for 48 hours. The solvent was evaporated and the residue purified by preparative TLC then dissolved in methanol (5 ml). Hydrogen chloride in methanol (0.5 ml) was added and the mixture stirred at room temperature for 16 hours. The solvent was then evaporated and the pH of the residue was adjusted to 7-8 by addition of sodium bicarbonate solution. The product was extracted into ethyl acetate and the extract was evaporated and the residue purified by preparative HPLC to give the title compound (16 mg).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 48 hours
  3. customThe solvent was evaporated
  4. customthe residue purified by preparative TLC
  5. dissolutionthen dissolved in methanol (5 ml)
  6. additionHydrogen chloride in methanol (0.5 ml) was added
  7. customThe solvent was then evaporated
  8. additionthe pH of the residue was adjusted to 7-8 by addition of sodium bicarbonate solution
  9. extractionThe product was extracted into ethyl acetate
  10. customthe extract was evaporated
  11. customthe residue purified by preparative HPLC

Sources & evidence

ORD record
ord-7b2a7038d7d84095b7a7bb4b43d3c3c4
Source dataset
uspto-grants-2016_01
Patent number
US09233962B2

Reaction notes

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